Cas no 88642-46-0 (Cerebroside B)

Cerebroside B structure
Cerebroside B structure
Product Name:Cerebroside B
CAS No:88642-46-0
MF:C41H77NO9
MW:728.051394224167
CID:837678
PubChem ID:11498616
Update Time:2024-12-09

Cerebroside B Chemical and Physical Properties

Names and Identifiers

    • Cerebroside B
    • (2R)-N-[(2S,3R,4E,8E)-1-(β-D-Glucopyranosyloxy)-3-hydroxy-9-methy l-4,8-octadecadien-2-yl]-2-hydroxyhexadecanamide
    • (2R)-N-[(1S,2R,3E,7E)-1-[(β-D-Glucopyranosyloxy)methyl]-2-hydroxy-8-methyl-3,7-heptadecadien-1-yl]-2-hydroxyhexadecanamide (ACI)
    • Hexadecanamide, N-[(1S,2R,3E,7E)-1-[(β-D-glucopyranosyloxy)methyl]-2-hydroxy-8-methyl-3,7-heptadecadienyl]-2-hydroxy-, (2R)- (9CI)
    • Hexadecanamide, N-[1-[(β-D-glucopyranosyloxy)methyl]-2-hydroxy-8-methyl-3,7-heptadecadienyl]-2-hydroxy-, [1S-[1R*(S*),2S*,3E,7E]]- (ZCI)
    • (4E,8E)-N-D-2′-Hydroxy-palmitoyl-1-O-B-D-glyco-pyranosyl-9-methyl-4,8-sphingadienine
    • (4E,8E)-N-D-2′-Hydroxypalmitoyl-1-O-β-D-glycopyranosyl-9-methyl-4,8-sphingadienine
    • 1-O-β-D-Glucopranosyl-(4E,8E)-2-[2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol
    • 1-O-β-D-Glucopyranosyl-(2S,3R,4E,8E)-2-[(2R)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol
    • 1-O-β-D-Glucopyranosyl-(2S,3R,4E,8E,2′R)-2-N-(2′-hydroxypalmitoyl)-9-methyl-4,8-sphingadienine
    • 1-O-β-D-Glucopyranosyl-2-N-(2′-D-hydroxyhexadecanoyl)-9-methylsphinga-4(E),8(E)-dienine
    • Cerebroside R 2
    • Cerebroside Sch II
    • N-2′-Hydroxypalmitoyl-1-O-β-D-glucopyranosyl-9-methyl-4E,8E-sphingadiene
    • GLXC-18815
    • 1-O-beta-d-glucopyranosyl-(2s,3r,4e,8e)-2-[(2r)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol
    • AKOS040760319
    • MS-31257
    • (2R)-N-[(1S,2R,3E,7E)-1-[(beta-D-Glucopyranosyloxy)methyl]-2-hydroxy-8-methyl-3,7-heptadecadien-1-yl]-2-hydroxyhexadecanamide
    • DTXSID201104435
    • HY-N3570
    • (2R)-2-hydroxy-N-[(2S,3R,4E,8E)-3-hydroxy-9-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]hexadecanamide
    • CHEBI:172811
    • CerebrosideB
    • CS-0023857
    • SCHEMBL161980
    • 88642-46-0
    • CHEMBL538217
    • (2R)-N-[(1S,2R,3E,7E)-1-[(I(2)-D-Glucopyranosyloxy)methyl]-2-hydroxy-8-methyl-3,7-heptadecadien-1-yl]-2-hydroxyhexadecanamide
    • [(2S,3R,4E,8E)-2-[[(2R)-2-Hydroxyhexadecanoyl]amino]-3-hydroxy-9-methyl-4,8-octadecadienyl]beta-D-glucopyranoside
    • Inchi： 1S/C41H77NO9/c1-4-6-8-10-12-13-14-15-16-18-20-24-29-35(45)40(49)42-33(31-50-41-39(48)38(47)37(46)36(30-43)51-41)34(44)28-25-21-23-27-32(3)26-22-19-17-11-9-7-5-2/h25,27-28,33-39,41,43-48H,4-24,26,29-31H2,1-3H3,(H,42,49)/b28-25+,32-27+/t33-,34+,35+,36+,37+,38-,39+,41+/m0/s1
    • InChI Key： YBSQGNFRWZKFMJ-FRJHFHMPSA-N
    • SMILES： O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)C[C@@H]([C@H](O)/C=C/CC/C=C(\C)/CCCCCCCCC)NC(=O)[C@H](O)CCCCCCCCCCCCCC

Computed Properties

  • Exact Mass: 727.56
  • Monoisotopic Mass: 727.56
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 9
  • Heavy Atom Count: 51
  • Rotatable Bond Count: 32
  • Complexity: 900
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 8
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 2
  • Topological Polar Surface Area: 169A^2
  • XLogP3: 10.2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.1±0.1 g/cm3
  • Boiling Point: 876.5±65.0 °C at 760 mmHg
  • Flash Point: 483.9±34.3 °C
  • PSA: 168.94000
  • LogP: 6.91500
  • Vapor Pressure: 0.0±0.6 mmHg at 25°C

Cerebroside B Security Information

Cerebroside B Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
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Cerebroside B Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium methoxide Solvents: Methanol ,  Tetrahydrofuran ;  0 °C; 2.5 h, 0 °C → rt; rt → 0 °C
1.2 Reagents: Acetic acid ;  0 °C
Reference
Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements
Black, Fiona J.; Kocienski, Philip J., Organic & Biomolecular Chemistry, 2010, 8(5), 1188-1193

Production Method 2

Reaction Conditions
1.1 Reagents: Sodium methoxide Solvents: Methanol ,  Tetrahydrofuran ;  2 h, 5 - 10 °C
1.2 Reagents: Acetic acid Solvents: Water ;  5 - 10 °C
Reference
Efficient stereocontrolled synthesis of sphingadienine derivatives
Murakami, Teiichi; Hirono, Reiko; Furusawa, Kiyotaka, Tetrahedron, 2005, 61(39), 9233-9241

Production Method 3

Reaction Conditions
1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
Reference
Synthesis of sphingosine relatives. III. Synthesis of (4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-9-methyl-4,8-sphingadienine, the fruiting-inducing cerebroside in a basidiomycete Schizophyllum commune
Mori, Kenji; Funaki, Yuji, Tetrahedron, 1985, 41(12), 2379-86

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Cerebroside B Preparation Products

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